Ayende @ Rahien

My name is Oren Eini
Founder of Hibernating Rhinos LTD and RavenDB.
You can reach me by phone or email:


+972 52-548-6969

, @ Q c

Posts: 6,026 | Comments: 44,842

filter by tags archive

Enough is enough: iTunes got to go

time to read 1 min | 123 words

Here is the story, the only reason that I am using iTunes is because I want to sync books that I buy from audible.com to my iPhone.

I am still fighting this problem. And I have installed / uninstalled, danced the mamba and even try some chicken sacrifice on the last full moon. Nothing helps, oh, it will works once, immediately after I install it, but on the next reboot, it will show the same error.

Right now I have uninstalled iTunes from my system, and I am currently building a VM specifically so I would be able to sync new audiobooks to my iPhones. I think that this is insane.

Anyone got a better option than that?



You've got it all wrong. You're supposed to sacrifice a goat, not a chicken!

Khalid Abuhakmeh

I ran into the same issue when trying to sync podcasts, what I ended up doing was just using iTunes on the my iPhone and downloaded what I wanted directly from the web. It's not the best option but it always works. More than i can say for iPoop.


I got a better option. Dump the f@$# iPhone and buy and Android :)


luckily you have a better option if you are an audible subscriber. Just download the Audible app, and you can download books directly to the phone over Wi-Fi, no iTunes involved. Frankly, just jumped to WP7 and am cutting the iTunes cord completely (not Audible support on WP7 yet though...)


If you have them as PDF files you can install Discover or iFiles lite, upload them via wifi to your iphone and view them in the PDF reader...

pete w

There is an open source winamp plugin on source forge I use for this kind of thing. It works for most ipods, not sure about iphones but might be worth looking at if you use winamp



My children want ipod touches for the big commercial holiday coming in december.

Sadly, the only reason I am pushing back on this is because it would mean installing iTunes for them, then maintaining and supporting it's insanity. I really like the iPod Touch as a device.... but iTunes on windows is insanely bad. Just horrible.


I'm using MediaMonkey instead. it's free and works fine.


I've tried iTunes in a VM before and it didn't work. If I remember correctly it had something to do with drivers. Basically the VM didn't recognize the iPod correctly. That was about 6 months ago so things my have improved. I'd be interested to know if it works for you.



High five! :]


+1 for MediaMonkey


In my experience this isn't an Apple problem so much as it's a persistent and pernicious Windows problem and why I eventually just gave up on it four or five years ago. First for Ubuntu, now for OS X.

Most of this type of goofy, pointless system fiddling has largely gone away.

junior programmer

I completely switched from Windows to Mac OS X but this switch so far is strictly for home use only because at the moment I am sort of 'stuck' on the .NET platform. I will be looking for ways to switch to non-Windows development in the future.

I actually wanted to know why Ayende sticks around .NET platform consider that a lot of his works are open source and open source in .NET community isn't particular good compared to other platforms. Or is it because the lack of open source efforts in .NET community makes it easy to provide commercial support to open source projects?


Apple definitely loses some points here for an obviously wrong dialog box. I recently came across a nearly identical problem related to Windows Live Photo Gallery. I was getting a message that a component was missing to view images that seemed unsolvable after trying everything.

That aside, generally, syncing to iTunes works for most users, so the problem is definitely solveable. If you're still interested in getting iTunes working instead of going with the alternates, here are a few things that come to mind to try to figure out the problem:

  1. Does the syncing work on another computer with a fresh install of Windows, all of the latest updates, and the latest version of iTunes? If it works, then a hardware problem can be ruled out.

  2. Start installing all of the software you use on your current machine on the new machine. Does the syncing still work after installing each one? If it still worked, then you can rule out major conflicts of your software. I can't say I've ever come across a major incompatibility between iTunes and other software, but I am sure that some examples exist, such as hardware drivers, virus scanners, utilities, etc.

  3. Still stumped? Your current Windows installation is therefore in a weird state and this problem will be the first of many more similar ones. Without the need to point fingers at what software problem caused the problem, a Windows reinstallation will solve the problem.

Then complain to Apple for having such a lousy error dialog.


I feel your pain. I tried and tried with iTunes but it was forever wreaking havoc.

Call me cynical, but I suspect the quality control on Windows iTunes is stepped down a bit to make people think it'll be better to just buy a Mac.

@CausticMango - I imagine running iTunes on Windows 95 was a bitch.


another +1 for sharepod. works great.


Whats wrong with the .NET platform?

junior programmer

@Graham, what do you use to connect your WP7 to PC? Yes... it's called crap ware.

junior programmer

WP7 is as bad as Symbian based smart phones at this point in time.


I installed iTunes on my 5 year old laptop. The only instance of iTunes in my whole house. So to sync, I connect to the old laptop. No way I allow iTunes invest the rest of my house.


I dual-boot my MBP and run iTunes and all my productivity software on OS X. You did buy an MBP, right? ;)

Ayende Rahien


Thank you, this solution works beautifully

Nigel Holland

I use Calibre for all my ebook managment, will sync to iPhone/iPad, will sync wirelessly with Stanza. It's free and open source.


Nigel Holland

Oops, should have realise that audible.com are audio books not ebooks.

Dan B

My company phone is an iPhone, which means i have no choice but to use iTunes to sync it and keep it up to date - so far I have used it in both VMWare and MS Virtual PC to keep iTunes from taking over my computer and both have worked fine for me.


Sadly, there's only one solution to these kinds of problems, boycott such products. Why oh why does these problems even exists, so sad so sad. :)


ohh yeh I feel your pain, iTunes is rubbish and extremely slow even on mac.


http://www.i-funbox.com/ - free, exposes entire file system

http://www.xilisoft.com/iphone-transfer.html - not free, but handles iTunes synching rather than direct file system access

Between these two i've had no need for iTunes any more... and best of all both allow you to access YOUR files without threatening to delete everything every time you swap computers!


Ugh! I know the feeling. The only reason I use Windows anymore is my iPad. :-|. Best of luck to you...

Julian Dominguez

+1 for MediaMonkey. Although it uses iTunes services under the hood, so not sure if it'll work for you or not.


Buy an android. The iPhone is a piece of junk.

Michael J. Ryan

I have to suggest again, what others have... Winamp tends to be my player of choice... Not sure if there are plugins for current iOS based iPods (Touch/Phone), but I used it in the past when I had my Gen3 iPod, and worked great.


Use the Audible iPhone app instead of iTunes -- It'll download the books OTA and has a nice player too.


Forgive me if this isn't feasible (I don't use iTunes, nor own an iPhone) but if they're basically just files I'd suggest having a look at dropbox ( https://www.dropbox.com/anywhere) which now has an iPhone app.

Shawn Wheatley

Do you really need them on your PC? I personally use the Audible.com app for the iPhone and download them directly to the phone. I almost never listen to them on my PC anyway, and you could always use Audible's manager software anyway. Pretty much the only time I plug my iPhone into my laptop anymore is when I want to take a backup.


What if you email yourself the epub file? the iPhone should be able to open it and you should find a button to import to iBooks

Comment preview

Comments have been closed on this topic.


No future posts left, oh my!


  1. Technical observations from my wife (3):
    13 Nov 2015 - Production issues
  2. Production postmortem (13):
    13 Nov 2015 - The case of the “it is slow on that machine (only)”
  3. Speaking (5):
    09 Nov 2015 - Community talk in Kiev, Ukraine–What does it take to be a good developer
  4. Find the bug (5):
    11 Sep 2015 - The concurrent memory buster
  5. Buffer allocation strategies (3):
    09 Sep 2015 - Bad usage patterns
View all series


Main feed Feed Stats
Comments feed   Comments Feed Stats